Synthesis, biological activity and modelling studies of two novel anti HIV PR inhibitors with a thiophene containing hydroxyethylamino core
Synthesis, biological activity and modelling studies of two novel anti HIV PR inhibitors with a thiophene containing hydroxyethylamino core
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DOI：
10.1016/j.tet.2005.04.048
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发表时间：
2005-07-04
期刊：
影响因子：
2.1
通讯作者：
Campaner, P
中科院分区：
文献类型：
--
作者：
Bonini, C;Chiummiento, L;Campaner, P
本文介绍了一种合成具有叠氮基、羟基和酯基功能的多功能中间体的有效方法，它是一种有用的拟肽化合物的前体。该合成的两个主要特征是在噻吩丙烯酸酯上使用Sharpless不对称二羟基化和随后通过环状亚硫酸盐的叠氮化钠进行区域选择性开环。叠氮醇的高度化学选择性还原产生了一种关键化合物，该化合物用于合成两种商业抗HIV PR类似物，例如奈非那韦和沙奎那韦。对这两种新的潜在药物的生物活性和分子模拟研究进行了评价。(c)2005爱思唯尔有限公司保留所有权利。
An efficient method has been developed for the synthesis of a versatile intermediate hearing azido, hydroxyl and ester functions, a useful precursor for peptidomimetic compounds. The two main features for this synthesis were the use of the Sharpless asymmetric dihydroxyiation on thiophene acrylate and the subsequent regioselective ring opening by sodium azide of the cyclic sulfite. Highly chemoselective reduction of the azido alcohol led to a key compound which was utilized for the synthesis of two analogues of commercial anti HIV PR such as nelfinavir and saquinavir. The biological activity and molecular modelling study on these two new potential drugs have been evaluated. (c) 2005 Elsevier Ltd. All rights reserved.